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1,3-Dimethyl-2-imidazolidinone → 4-Methoxy-2-methylquinolin-8-OL

HRID 564926
Notes
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Reaction equation

HRID 564926 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.CN1CCN(C)[C:16]1=[O:21].C[O-].[Na+]>CO>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[O:21][CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 10942334Sodium MethoxideHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 183218914-Methoxy-2-methylquinolin-8-OL

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-8-hydroxy-2-methylquinoline (9 g), 1,3-dimethyl-2-imidazolidinone (100 ml) and 28% solution of sodium methoxide in methanol (135 ml) was stirred at 150° C. for 4 hours. The reaction mixture was cooled to ambient temperature followed by partition into ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The crystalline residue was washed with n-hexane to give 8-hydroxy-4-methoxy-2-methylquinoline (5.57 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customby partition into ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe crystalline residue was washed with n-hexane

Sources & evidence

ORD record
ord-c67fb0c56a1845a78f191339042bb2c6
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06169095A

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes